ArticleJournal of the American Chemical Society2021
Cooperative Hydrogen-Bond-Donor Catalysis with Hydrogen Chloride Enables Highly Enantioselective Prins Cyclization Reactions.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 36 citations in OpenAlex.
- Chemo-, Diastereo-, and Enantioselective Radical Cyclization of Enals to Access Cyclopentanols Bearing an α-Quaternary Center.Angewandte Chemie (International ed. in English) · 2026Article
- Catalytic Ring Opening of Epoxides by Metal Triflates: Influence of a Pending Olefin.Molecules (Basel, Switzerland) · 2026Article
- E/Z Isomerization-Enabled Conversion from Dual-Carbon to Single-Carbon Insertion into an Aromatic System.JACS Au · 2026Article
- An anion-binding approach to enantioselective photoredox catalysis.Science (New York, N.Y.) · 2025Article
- Article
- Catalytic Asymmetric (Journal of the American Chemical Society · 2025Article
- Selective Noncovalent Catalysis with Small Molecules.Chemical reviews · 2025Review
- On the gold(I)-catalyzed enantioselective addition of indole to diphenylallene via anion-binding catalysis.Tetrahedron letters · 2024Article
- Dual-Hydrogen-Bond Donor and Brønsted Acid Cocatalysis Enables Highly Enantioselective Protio-Semipinacol Rearrangement Reactions.Journal of the American Chemical Society · 2023Article
- Article
- Mechanism of a Dually Catalyzed Enantioselective Oxa-Pictet-Spengler Reaction and the Development of a Stereodivergent Variant.ACS catalysis · 2023Article
- Recent Developments and Trends in Asymmetric Organocatalysis.European journal of organic chemistry · 2023Review
- Exploring Structure-Function Relationships of Aryl Pyrrolidine-Based Hydrogen-Bond Donors in Asymmetric Catalysis Using Data-Driven Techniques.ACS catalysis · 2022Article
- Evidence for Oxonium Ions in Ethereal "Hydrogen Chloride".Organic letters · 2022Article
- Chloride-Mediated Alkene Activation Drives Enantioselective Thiourea and Hydrogen Chloride Co-Catalyzed Prins Cyclizations.Journal of the American Chemical Society · 2022Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Cooperative asymmetric catalysis with hydrogen chloride (HCl) and chiral dual-hydrogen-bond donors (HBDs) is applied successfully to highly enantioselective Prins cyclization reactions of a wide variety of simple alkenyl aldehydes. The optimal chiral catalysts were designed to withstand the strongly acidic reaction conditions and were found to induce rate accelerations of 2 orders of magnitude over reactions catalyzed by HCl alone. We propose that the combination of strong mineral acids and chiral hydrogen-bond-donor catalysts may represent a general strategy for inducing enantioselectivity in reactions that require highly acidic conditions.
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